TW200415139A - Ionic liquids containing borate or phosphate anions - Google Patents
Ionic liquids containing borate or phosphate anions Download PDFInfo
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- TW200415139A TW200415139A TW092118064A TW92118064A TW200415139A TW 200415139 A TW200415139 A TW 200415139A TW 092118064 A TW092118064 A TW 092118064A TW 92118064 A TW92118064 A TW 92118064A TW 200415139 A TW200415139 A TW 200415139A
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- Prior art keywords
- ionic liquid
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 89
- -1 phosphate anions Chemical class 0.000 title claims description 26
- 229910019142 PO4 Inorganic materials 0.000 title abstract 2
- 239000010452 phosphate Substances 0.000 title abstract 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title description 8
- 239000004327 boric acid Substances 0.000 claims abstract description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 4
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 150000001450 anions Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical group 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 23
- 150000001768 cations Chemical class 0.000 claims description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052698 phosphorus Chemical group 0.000 claims description 18
- 239000011574 phosphorus Chemical group 0.000 claims description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 229910052796 boron Inorganic materials 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 14
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000007857 hydrazones Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052705 radium Inorganic materials 0.000 claims description 3
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229940098465 tincture Drugs 0.000 claims 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 5
- 241000219112 Cucumis Species 0.000 claims 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 2
- 125000001317 arsoryl group Chemical group *[As](*)(*)=O 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 210000000078 claw Anatomy 0.000 claims 1
- 125000005469 ethylenyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052702 rhenium Chemical group 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 229910052716 thallium Inorganic materials 0.000 claims 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 abstract 1
- 238000005649 metathesis reaction Methods 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 230000002209 hydrophobic effect Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 229960004889 salicylic acid Drugs 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical group CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- NPEZLHFSGWLIQZ-UHFFFAOYSA-N lithium;bis[(2-hydroxyphenyl)methoxy]borinate Chemical compound [Li+].OC1=CC=CC=C1COB([O-])OCC1=CC=CC=C1O NPEZLHFSGWLIQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DYMVSGILVVGDIZ-UHFFFAOYSA-N bis[(2-hydroxyphenyl)methoxy]borinic acid Chemical compound C=1C=CC=C(O)C=1COB(O)OCC1=CC=CC=C1O DYMVSGILVVGDIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- QBXRBEKWYINGBR-UHFFFAOYSA-N lithium;bis[(2-hydroxy-3-methylphenyl)methoxy]borinate Chemical compound [Li+].CC1=CC=CC(COB([O-])OCC=2C(=C(C)C=CC=2)O)=C1O QBXRBEKWYINGBR-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- TURNUGGYWFMARH-UHFFFAOYSA-N triethyl(methyl)azanium;borate Chemical compound [O-]B([O-])[O-].CC[N+](C)(CC)CC.CC[N+](C)(CC)CC.CC[N+](C)(CC)CC TURNUGGYWFMARH-UHFFFAOYSA-N 0.000 description 2
- VKPWUPHIAVTZRB-UHFFFAOYSA-N trilithium;benzene-1,2-diol;borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-].OC1=CC=CC=C1O.OC1=CC=CC=C1O VKPWUPHIAVTZRB-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical group CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- ILQHIGIKULUQFQ-UHFFFAOYSA-N 1-dodecyl-3-methylimidazolium Chemical group CCCCCCCCCCCCN1C=C[N+](C)=C1 ILQHIGIKULUQFQ-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
- WEZNMMBMSZOXAZ-UHFFFAOYSA-N 2-boronooxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOB(O)O WEZNMMBMSZOXAZ-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- QZEWCQGGAIGUPS-UHFFFAOYSA-N benzene-1,2-diol;boric acid Chemical compound OB(O)O.OC1=CC=CC=C1O.OC1=CC=CC=C1O QZEWCQGGAIGUPS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KPZIWGUXCQLIAA-UHFFFAOYSA-N bis(2,3-dihydroxyphenoxy)borinic acid Chemical compound B(O)(OC1=CC=CC(=C1O)O)OC2=CC=CC(=C2O)O KPZIWGUXCQLIAA-UHFFFAOYSA-N 0.000 description 1
- VSTXFLSMBOUSSA-UHFFFAOYSA-N bis[(2,4-dihydroxyphenyl)methoxy]borinic acid Chemical compound B(O)(OCC1=C(C=C(C=C1)O)O)OCC2=C(C=C(C=C2)O)O VSTXFLSMBOUSSA-UHFFFAOYSA-N 0.000 description 1
- KKMYTFUPBRHJLV-UHFFFAOYSA-N bis[(2-hydroxy-3-methylphenyl)methoxy]borinic acid Chemical compound CC1=CC=CC(COB(O)OCC=2C(=C(C)C=CC=2)O)=C1O KKMYTFUPBRHJLV-UHFFFAOYSA-N 0.000 description 1
- KWMMUDHWNUULTA-UHFFFAOYSA-N bis[(2-hydroxyphenyl)methoxy]borinate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.OC1=CC=CC=C1COB([O-])OCC1=CC=CC=C1O KWMMUDHWNUULTA-UHFFFAOYSA-N 0.000 description 1
- 239000002639 bone cement Substances 0.000 description 1
- UDHQWZLOKFJXDG-UHFFFAOYSA-N boric acid 2-hydroxybenzoic acid Chemical compound B(O)(O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O UDHQWZLOKFJXDG-UHFFFAOYSA-N 0.000 description 1
- ARTGXHJAOOHUMW-UHFFFAOYSA-N boric acid hydrate Chemical compound O.OB(O)O ARTGXHJAOOHUMW-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 229940075419 choline hydroxide Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- MWVMKRRNRAEZOI-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCN(C)CCCC MWVMKRRNRAEZOI-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- AMCYFOSVYJWEBU-UHFFFAOYSA-N tetrabutylazanium borate Chemical compound [O-]B([O-])[O-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC AMCYFOSVYJWEBU-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/188,452 US20040007693A1 (en) | 2002-07-03 | 2002-07-03 | Ionic liquids containing borate or phosphate anions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200415139A true TW200415139A (en) | 2004-08-16 |
Family
ID=30114010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092118064A TW200415139A (en) | 2002-07-03 | 2003-07-02 | Ionic liquids containing borate or phosphate anions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20040007693A1 (fr) |
| AU (1) | AU2003247887A1 (fr) |
| TW (1) | TW200415139A (fr) |
| WO (1) | WO2004005222A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103429719A (zh) * | 2011-03-22 | 2013-12-04 | 奥列格·N·安祖肯 | 基于离子液体的润滑剂以及包含离子的润滑添加剂 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040077519A1 (en) * | 2002-06-28 | 2004-04-22 | The Procter & Gamble Co. | Ionic liquid based products and method of using the same |
| TW200526587A (en) * | 2003-09-05 | 2005-08-16 | Univ Alabama | Ionic liquids containing secondary hydroxyl-groups and a method for their preparation |
| DE102004003958A1 (de) * | 2004-01-26 | 2005-08-11 | Basf Ag | Herstellungsmethode für ionische Flüssigkeiten |
| GB0422447D0 (en) * | 2004-10-08 | 2004-11-10 | Univ Cambridge Tech | Use of ionic liquids |
| US7776810B2 (en) * | 2004-11-01 | 2010-08-17 | The Procter & Gamble Company | Compositions containing ionic liquid actives |
| US20060094621A1 (en) * | 2004-11-01 | 2006-05-04 | Jordan Glenn T Iv | Process for improving processability of a concentrate and compositions made by the same |
| US20060090777A1 (en) * | 2004-11-01 | 2006-05-04 | Hecht Stacie E | Multiphase cleaning compositions having ionic liquid phase |
| US20060094616A1 (en) * | 2004-11-01 | 2006-05-04 | Hecht Stacie E | Ionic liquids derived from surfactants |
| US7737102B2 (en) * | 2004-11-01 | 2010-06-15 | The Procter & Gamble Company | Ionic liquids derived from functionalized anionic surfactants |
| US20060090271A1 (en) * | 2004-11-01 | 2006-05-04 | Price Kenneth N | Processes for modifying textiles using ionic liquids |
| US7939485B2 (en) * | 2004-11-01 | 2011-05-10 | The Procter & Gamble Company | Benefit agent delivery system comprising ionic liquid |
| US7786065B2 (en) * | 2005-02-18 | 2010-08-31 | The Procter & Gamble Company | Ionic liquids derived from peracid anions |
| WO2006125175A2 (fr) * | 2005-05-19 | 2006-11-23 | University Of South Alabama | Liquides ioniques a base d'ions de boronium et leurs procedes de production |
| US7282468B2 (en) * | 2005-07-18 | 2007-10-16 | Carestream Health Inc. | Direct thermographic materials with catechol borate reducing agents |
| US8232265B2 (en) | 2005-10-07 | 2012-07-31 | Board Of Trustees Of The University Of Alabama | Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients |
| US8118916B2 (en) * | 2005-10-21 | 2012-02-21 | The University Of Cincinnati | High capacity materials for capture of metal vapors from gas streams |
| DE102008041748A1 (de) * | 2007-08-30 | 2009-03-05 | Chemetall Gmbh | Sauerstoffverbindung der Borgruppe |
| FR2930247B1 (fr) | 2008-04-21 | 2012-12-07 | Commissariat Energie Atomique | Sels d'onium et leur utilisation pour la detection et le dosage des metaux. |
| WO2016040629A1 (fr) | 2014-09-10 | 2016-03-17 | Basf Se | Composition de nettoyage encapsulée |
| EP3262144B1 (fr) | 2015-02-26 | 2024-05-08 | The Lubrizol Corporation | Composés borates tétraédriques aromatiques pour compositions lubrifiantes |
| US10479804B2 (en) | 2016-02-05 | 2019-11-19 | Gotion Inc. | Preparation of ammonium or phosphonium borate salts |
| JP2019512575A (ja) | 2016-03-09 | 2019-05-16 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | カプセル化された洗濯洗浄用組成物 |
| JP7382969B2 (ja) * | 2018-05-30 | 2023-11-17 | トータルエナジーズ マーケティング サービシーズ | 第四級モノアンモニウム官能基、酸性官能基およびホウ素官能基を含む化合物、ならびにその潤滑剤添加物としての使用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539614A (en) * | 1966-02-07 | 1970-11-10 | Sprague Electric Co | Quaternary ammonium diorganoboron compounds |
| US3403305A (en) * | 1966-11-10 | 1968-09-24 | Sprague Electric Co | Electrolytic capacitor having an electrolyte containing a borate coordination compound |
| US4611013A (en) * | 1984-06-12 | 1986-09-09 | Bp Chemicals Limited | Catalysts for the preparation of carbodiimide foams and elastomers |
| JPH083666B2 (ja) * | 1986-03-07 | 1996-01-17 | 富士ゼロックス株式会社 | トナ−組成物 |
| GB8723603D0 (en) * | 1987-10-08 | 1987-11-11 | British Petroleum Co Plc | Polyketones |
| DE4316104A1 (de) * | 1993-05-13 | 1994-11-17 | Manfred Wuehr | Elektrolyt zur Anwendung in einer galvanischen Zelle |
| DE10026565A1 (de) * | 2000-05-30 | 2001-12-06 | Merck Patent Gmbh | Ionische Flüssigkeiten |
-
2002
- 2002-07-03 US US10/188,452 patent/US20040007693A1/en not_active Abandoned
-
2003
- 2003-07-02 TW TW092118064A patent/TW200415139A/zh unknown
- 2003-07-03 WO PCT/US2003/021125 patent/WO2004005222A2/fr active Application Filing
- 2003-07-03 AU AU2003247887A patent/AU2003247887A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103429719A (zh) * | 2011-03-22 | 2013-12-04 | 奥列格·N·安祖肯 | 基于离子液体的润滑剂以及包含离子的润滑添加剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040007693A1 (en) | 2004-01-15 |
| AU2003247887A8 (en) | 2004-01-23 |
| WO2004005222A2 (fr) | 2004-01-15 |
| AU2003247887A1 (en) | 2004-01-23 |
| WO2004005222A3 (fr) | 2004-09-23 |
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